HCID 11011640, compound → 3-Phenylindole

HRID 1585219Notes

Reaction equation

S(N1CCC[C@@H]1C(Cl)=O)(C1C=CC(C)=CC=1)(=O)=O.[C:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27](C(=O)[C@H]3CCCN3S(C3C=CC(C)=CC=3)(=O)=O)[CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Reactant 2

HCID 11011640HCID 11011640, compound

HCID 15428727HCID 15428727, compound

Product 1

HCID 965023-PhenylindoleYield 207.5%

Conditions

Temperature: -40 °C

Procedure

By following the procedure of Example 1 substantially faithfully while using N-tosyl-D-prolyl chloride in the place of benzoyl chloride and changing the reaction temperature during the course of cooling to -40° C., 3.88 g of 3-phenyl-1-(N-tosyl-D-prolyl)indole (48.2%) having a melting point of 148-149° C. was obtained from 3.50 g of 3-phenylindole.

Sources & evidence

ORD record: ord-81d4534ea3bc42b5a5dff312efc2db15
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05936098

Reaction notes

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